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Conch Shell

3 Bedrooms
1 Bath
6 Guests
Piney Island
Waterfront
Internet
Outdoor Shower

The house is located on Pine Drive in Piney Island - the closest neighborhood to the beach - convenient for shopping and dining on Maddox Blvd. This wonderful waterfront beach bungalow features a wrap around deck with views of Assateague and the light house. You can bring your boat, jet skis or kayaks and keep them tied up out front. There is a spacious living room for entertaining and a nicely remodeled kitchen! Your rental also includes water access (a short walk from the home) to a tidal creek that comes up from Oyster Bay - it's a great place for the kids to crab or to launch a kayak or canoe. 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted on the premises. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Horseshoe Hideaway

3 Bedrooms
2 Baths
8 Guests
In Town
Gas Grill
Screened Porch
Internet

Located in a secluded neighborhood, in the middle of town, 'Horseshoe Hideaway' is comfortably situated back off of a back road, fully enclosed by a fence, and ensconced by a generous yard and mature wooded area. With all the convenience of traveling around the island with ease, this home allows guests to drive or bike to Maddox Blvd, the beach or to the Main Street shops within minutes. Enjoy the outdoors on the fully screened in porches located on both the front and the back of the home, or take advantage of the generous back deck (accessed by a ramp or stairs) and supplied with a large gas grill, picnic table and Adirondack chairs. Inside the home features 3 bedrooms and 2 full bathrooms, a separate dining room, living room and eat in kitchen. There are several seating areas where guests can spread out or congregate as a group. The home is appointed with everything you need to enjoy a vacation at the Beach. This cute-as-a-button rancher home is waiting for your family vacation! Clean, comfortable and modest best describe the single-level home; there's an open kitchen, living and dining area that opens up to a front AND back screened porch. Enjoy all of the outdoor space from one of the 2 screened porches, or the spacious back deck and back yard! Located on a side street just off of Ridge Road, 'Horseshoe Hideaway' is conveniently located just minutes from downtown Chincoteague, as well as the "Beach Road." Come and check it out for yourself!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Sunset Bay Villa 119

3 Bedrooms
2 Baths
8 Guests
Sunset Bay
Waterfront
Pool
Internet

Immerse yourself in luxury for days at this pristine waterfront villa! This condo unit provides the most spectacular views of the Chincoteague Bay, coupled with some unforgettable sunsets. Sunset Bay Villa 119 offers first floor living throughout with easy access to the condo amenities. Not to mention, convenient walk-out access to the marina boardwalk and boat dock. An open floor plan, including lots of windows that boast those beautiful bay views! Upon entering you will find two bedrooms- One is furnished with two twin bunks, as well as a TV. The 2nd bedroom features a queen size bed and also offers a spectacular waterfront view. There is a shared bathroom with a tub/shower combo in the hall, as well as a washer and dryer in the laundry room. As you make your way further into your beach abode, you will find a large open kitchen featuring granite countertops, BRAND NEW stainless steel appliances, and all the essential cookware to prepare delicious meals during your stay. The primary en suite is situated so as to fully encompass the most captivating water views, while also offering a luxury bathroom with a tiled shower and jacuzzi tub. Enjoy a relaxing evening beverage while sitting on the balcony watching the sun set, or a nice cup of coffee in the morning. The balcony is accessible from both the primary bedroom suite and the open living area.  Enjoy the convenience of close-by restaurants, shops, movie theater and much more with the poximity of Sunset Bay to the Downtown Chincoteague area. ** NEW FOR 2025: Brand new appliances, new flooring and other upgrades! You won't be disappointed! **

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Avalon

4 Bedrooms
2 Baths & 1 Half
10 Guests
Oyster Bay
Waterfront
Screened Porch
Internet
Outdoor Shower

Avalon is a charming 4 bedroom, 2.5 bathroom home situated on a bulkheaded waterfront lot on Oyster Bay! There is a large great room that boasts two family rooms, a dining area and large kitchen. From the gas fireplace, to the 16' cathedral knotted pine ceilings, this home is bright, warm and inviting. Avalon offers two queen bedrooms with screened porch access (one private) and two twin bedrooms. Offering over 600 sq. ft. of screened porch - you could live outdoors! The first level also offers a full size futon and 1/2 bath. Avalon is one of our most popular offerings; it books quickly! 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted on the premises. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Trembling Bay

3 Bedrooms
2 Baths
6 Guests
North Main
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet

This beautifully renovated 3 bedroom, 2 bath Chincoteague cottage is nestled along the salt marshes in a natural setting on Chincoteague Bay. A few of the fine features include a private pier, a new kitchen & appliances, waterside screen porch & deck, and private master bedroom suite with a custom-designed luxurious bath. The numerous windows and over-sized sliding doors allow panoramic water views from nearly any spot in the house. The first floor is completely wheelchair accessible and features your main living areas, large master bedroom suite (K) with bathroom, and second full bathroom with shower/tub. Upstairs features the second and third bedrooms (D/2T). If relaxation is what you're seeking, look no further. This quiet, peaceful location at the water's edge will delight the senses. Come and see for yourself; you won't be disappointed!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pet Friendly with a fee, No cats, 2 dogs max. ($150 per pet) 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Grey Heron

3 Bedrooms
2 Baths
8 Guests
North Main
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Gas Grill
Screened Porch
Internet
Outdoor Shower

Majestic views await you from every room at Grey Heron, a charming raised contemporary located on North Main Street. Enjoy the unparalleled island sunsets from the private dock, spacious screened in porch and dining area, or with it's floor to ceiling windows and numerous cozy seating areas - from anywhere else in the home! Vintage artwork from local artist Hall Lott, known for his cover artwork for the Chincoteague Island Easter & Decoy Festival and Pony Swim posters, adorn the walls at every turn. Plush, cozy furniture in the living area as well as a round-about room featuring stunning 180-degree views of Chincoteague Bay and salt marsh give you plenty of space to enjoy company comfortably. A fully equipped kitchen (range, dishwasher, refrigerator) to prepare meals for family and friends, which is connected to the great room featuring a beautiful working fireplace and natural wooden floors. Grey Heron features 3 bedrooms, each boasting their own private balcony. On the upper level (accessible by the spiral staircase in the great room) you'll find the master bedroom - with the largest balcony, overlooking the sweeping vista of the bay and marsh. A comfortable king sized bed and television, as well as a full bath. The floor to ceiling bay window delivers plenty of natural island sunshine into the bedroom. Downstairs you will find the other two bedrooms - both with queen sized beds, a small balcony, and a cozy sitting area with view of the bay and marsh. Bring your bushel basket and crab right off the dock, then enjoy the bounty of the Chincoteague Bay from the screened-in porch. Bring your kayaks as well and launch them right from the private launch found off the bulkhead on the property. An outdoor shower to hose off after a sandy day at the beach. Plenty of space outside to enjoy family activities, and pet-friendly so bring your furry friends - they love basking in the sun on the dock as much as people do!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Beach Bungalow

3 Bedrooms
3 Baths
11 Guests
In Town
Waterfront
Pet Friendly
Charcoal Grill
Internet

This fabulous "Beach Bungalow" is waiting for you! Tucked away on the marshlands overlooking Oyster Bay and the East Side of the island is where you'll find this 3 bedroom cute-as-a-button cottage. There are fresh new upgrades, including a bathroom, a new laundry closet, and a new deck. The bright, natural sunlight streams into the rooms via skylights and the floor plan is open and inviting. The living room extends to the dining area, which is completely open to the kitchen. Off of the kitchen, you step down into a family room/bedroom with a full bathroom, futon fold-out bed, and a Twin pull-out sleeper chair. From the hallway off of the dining area, you'll find two more bedrooms, one with a new ensuite bathroom. There is a new washer/dryer closet and a full bathroom accessed in the hallway. The master bedroom will be your favorite spot in the house with large sliding doors on 3 sides and a fabulous, cozy sitting area overlooking the marshes and bay, it's perfect for unwinding after a day at the beach, or quietly starting your day. Conveniently located to Maddox Boulevard (Beach Road) and downtown Chincoteague Island you're only a few minutes from restaurants, shopping, movies, the beach, and more! The fabulous new deck will be another spot you will love to enjoy the beautiful views all day and night! There's room for everyone, even your pet(s)! Not to mention the fenced-in yard for your furry family member!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed before arrival. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Serenity at Deep Hole Hideaway

2 Bedrooms
1 Bath
6 Guests
In Town
Pet Friendly
Charcoal Grill
Internet

Welcome to your blissful oasis, "Serenity at Deep Hole Hideaway!" This charming haven has been given a complete makeover to cater to all your vacation dreams. The kitchen is stacked with top-notch gadgets to whip up that perfect meal. The living room features a cozy sleeper sofa to squeeze in a few extra guests. The main bedroom boasts a luxurious queen-sized bed, while the guest room offers a snug twin daybed, providing ample space for up to six guests. Step outside and relax on the deck, indulging in a long-awaited book. And, if you're in the mood for some classic campfire fun, gather around the firepit and toast up some scrumptious S'mores and hotdogs!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Dockside

3 Bedrooms
3 Baths & 1 Half
8 Guests
East Side
Waterfront
Boat Dock
Gas Grill
Internet

Located on the Assateague Channel, this is your chance to watch the ponies from your own deck. A wonderful panoramic view awaits you?to the left is the Assateague Bridge; to right of the bridge is the Assateague Lighthouse and ponies; and to the far right is Tom?s Cove and the ocean inlet. Come and fish from your own dock and tie your boat along side! Inside you will find central heat/air, 3 decks, all appliances, gas grill, satellite TV & DVD player and internet access. Enjoy evenings resting beside the wood fireplace (off-season).

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Starfish on the Channel

3 Bedrooms
2 Baths & 1 Half
9 Guests
South Main
Waterfront
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

Introducing a pristine rental opportunity at this newly-listed townhouse, offering a blend of modern amenities and serene waterfront living. Nestled in the charming town of Chincoteague Island, Virginia, this property promises comfort and luxury across its three beautifully appointed bedrooms and two and a half bathrooms.

Every corner of this townhouse whispers elegance, from the completely renovated interiors adorned with all-new stylish furniture and decor, to the luxury mattresses that promise a night of restorative sleep. Culinary enthusiasts will delight in the fully stocked chef's kitchen, equipped with an additional ice machine - perfect for entertaining or a quiet dinner at home.

The allure of this home extends beyond its walls, with outdoor living spaces that invite relaxation and connection with nature. Two waterside screened porches offer tranquil views and a gentle breeze off Chincoteague Bay, while a private screened porch off the primary bedroom suite offers a personal retreat.

For adventure seekers or those who enjoy the simple pleasure of a lazy day fishing, the property includes a long pier with boat dockage (as available), as well as fishing and crabbing supplies. Explore the local area with the two available bikes.

Local attractions enrich the living experience, with Downtown Chincoteague Waterfront Park, Curtis Merritt Harbor, and the undisturbed Assateague Beach mere minutes away. For a splash of fun, Maui Jack's Waterpark is also close by, ensuring entertainment options are plentiful.

This offering is not just a house, but a gateway to a lifestyle of leisure and luxury, beautifully intertwined with the convenience and charm of Chincoteague life. Ready to make your coastal living dream a reality? This townhouse is waiting to become your beach home away from home!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted on the premises. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

My Island Escape

3 Bedrooms
2 Baths
7 Guests
North Main
Water Access
Boat Dock
Charcoal Grill
Internet
Outdoor Shower

Tucked away on a quiet lane off of North Main is where you will find My Island Escape. This brand-new home is absolutely immaculate! Luxury finishings, tastefully appointed furniture and decor make for a flawless backdrop to your next vacation. The living room at My Island Escape features ample comfortable seating and a flat screen television, and flows into the fully equipped, gourmet, eat-in kitchen that features a large island and plenty of space for cooking, dining, and enjoying meals with the family. The master bedroom features a Queen size bed with an en suite highlighted by a large soaking tub, double vanity, and separate glass stand up shower. The two other bedrooms in the home are close by a full bathroom located off the hallway. Another bonus in this home is the spacious laundry room complete with a full-size washer and dryer, iron and an ironing board, and connects to a convenient half bath. Outside, you will find deck space with outdoor furniture, and a picnic table with umbrella for outdoor dining. If you are looking for a clean, relaxing, upscale rental with great attention to detail ? look no further and escape to My Island Escape!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Beach Haven

3 Bedrooms
2 Baths & 1 Half
9 Guests
In Town
Town & Country
Charcoal Grill
Internet

If you enjoy being close to town and activities, 'Beach Haven' is most likely your perfect spot! Located on just one block off of Main Street, this lovely home is conveniently located to downtown Chincoteague Island, the movie theater, restaurants, famous Island Creamery, adventure park and more! The wrap around second-level deck is nicely furnished and inviting - it's the ideal place to relax with a cup of coffee in the morning or a cool drink after a long day at the beach. 

As you enter this fantastic modern home, you're greeted by an open floor plan. The main level features the living room, kitchen with breakfast bar, dining room and half bath/powder room. The lower level is entirely a two-car garage that is accessible by guests; it's a wonderful place to store your bikes or beach gear! Upstairs you'll find 3 bedrooms and 2 full bathrooms, one of them being a master bedroom en suite. Two bedrooms feature a queen bed each, and the third (kid's) bedroom features a bunk bed (2 Doubles) and a Twin bed. 

Lets talk electronics! This home has been carefully and tastefully furnished for the discerning traveler. The living room and all 3 bedrooms all have large Smart TVs, and the kid's bedroom includes an HDMI cable for easily connecting gaming consoles, etc. You'll also enjoy amenities such as keyless self check-in and check-out.

Come for a week in the summer, or come for a shorter stay in the spring or fall. 'Beach Haven' is available year-round and the island is gorgeous the whole year through!

- No smoking is permitted on the premises.

- Linens and towels are included with your reservation.

- No pets are permitted on the premises. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

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